


Gripped Tight and Saved from the Douchewaffle Ex AKA Boss

by BabysNotaProp (SuzetteB)



Category: Supernatural
Genre: Abusive Relationships, Anal Sex, Angst and Hurt/Comfort, Bottom Dean, Come Eating, Destiel Promptober, Emotionally Hurt Dean Winchester, Episode: s04e17 It's a Terrible Life, Light Dom/sub, M/M, Promptober, Promptober 2018, Sandover Bridge & Iron Inc., Shameless Smut, Top Castiel
Language: English
Status: Completed
Published: 2018-10-20
Updated: 2018-10-21
Packaged: 2019-08-04 18:11:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 1,980
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16351595
Author URL: https://archiveofourown.org/users/SuzetteB/pseuds/BabysNotaProp
Summary: The man sitting at the desk across from Dean used to share a bed with him. He is a sadistic, abusive asshole from hell. At his lowest moment, a man who might be an actual angel swoops in and saves him.





	1. Chapter 1

**Author's Note:**

> I liked this more than I thought I would. Let me know if you find any parallels between this and the show! <3
> 
> Written for Destiel Promptober 2018: It’s a Terrible Life.

It was awkward enough that Dean’s ex interviewed him for the position at Sandover Bridge & Iron. He had to smile right at Michael and answer his questions cordially, as if all those years of mental abuse were supposed to melt away. He didn’t miss the smug grin on Michael’s face as he listed his qualifications, and wished he could reach across the desk and strangle him until he quit it with the evil smirk. 

 

That was awkward enough, but then Michael insisted on monthly one-on-one chats about individual growth, strengths and weaknesses, bla bla bla. It made Dean sick sitting across from him, hearing opportunities for improvement detailed so professionally from the person who did the same thing when they were together, except louder. And with manhandling, sometimes. 

 

In that moment, Dean realized it had been more than mental abuse. Michael didn’t lay a hand on him now because his office walls were made of glass. How very different their home life might’ve been if there had constantly been a visitor; a workmate; hell, a total  _ stranger _ so Michael would have someone to impress. 

 

“Are you alright?”

 

The unfamiliar voice shook him out of his daze. He paused from tapping his pencil on his mousepad and glanced up. The handsome new graphic design manager was leaning in his door frame, stirring coffee. He must’ve been daydreaming too much to hear him knock. 

 

“Uh, yeah,” Dean replied with a forced smile. “Just had a touch base with the boss, is all.” 

 

“The guys in graphics tell me this only started once you came on.”

 

Dean blinked. “What?”

 

“The frivolous and quite frankly offensive touch bases,” the man clarified as he strolled into Dean’s office. “I think he started them just because of you. Do you know each other?”

 

“He’s my ex,” Dean replied regretfully. 

 

The blue eyed graphic design manager waited for more, but the silence that filled the room told him all he needed to now. “Oh, I see. You should know, Mr. Smith, that if you believe this is harassment, you should report it to HR.”

 

“And get myself fired for reporting abuse?” Dean replied, the situation having replayed so many times in his head that he had been ready for a proposition like this for weeks. “He will know I’m the one who called him in. The guy is a psycho. He’ll either give me the boot or make me so miserable, I’ll want out.”

 

The man across from him looked down and pursed his lips thoughtfully. Being in graphic design, his interaction with people was mostly limited to his immediate circle, so he wasn’t quite sure what the situation called for. However, fear is a universal feeling, and he knew a way to help with that. 

 

“My name is Cas Milton,” he said as he looked back up.

 

“Nice to meet you, Cas.” The words rolled off his tongue with the ease of someone who’s recited canned phrases like that for a long time. 

 

“Next time you have a meeting with Michael, will you allow me to go with you?”

 

Dean clenched his jaw skeptically, looking hard and deep into Cas’ eyes. He saw no ill will or ulterior motive, and he was good at reading people. 

 

“You’d… you’d do that for me?”

 

“Of course.”

 

“Why?”

 

“Why not?”

 

“Because you don’t know me,” Dean deadpanned. “You don’t know what kind of person I am. Who are you to say I don’t deserve some of the crap that flies outta his mouth? You don’t know.”

 

“I do know,” Cas explained patiently, “that no one should have to feel uncomfortable at work because their ex is humiliating them from across a desk, in the name of workplace unity.”

 

Dean raised a brow curiously. 

 

“They didn’t just pick me up off the street, Dean.” Cas “I was over a lot of people at my last job. I came here for the pay, but I’m actually doing less now than I was before. I know how bosses think. Please let me help you.”

 

Dean nodded and a small but genuine smile tugged at his cheeks. “Thanks, Cas.”

 

“Mr. Smith,” Michael’s nauseating voice rang out from the cracked door. Dean sat up a little straighter as he entered. “I need to speak to you for a minute. Mr. Milton, would you mind giving us some privacy?”

 

Cas twisted in his seat, but didn’t leave the chair. “Actually, I think I’ll stay here. Dean and I were having a conversation we will probably resume after you leave, so whatever it is, don’t mind me, I’ll just be here waiting.”

 

Michael scoffed lightly. “No, Mr. Milton. You see, this is a matter of sales and marketing. The subject matter could be confidential to the company.”

 

“No it isn’t.”

 

Michael arched his brows, taken aback by the bold assumption. “Excuse me?”

 

Cas gave him a silent onceover, making sure to cause as much discomfort as possible nonverbally. “During our touch bases, you have a folder for each employee, which you didn’t bring. So it’s a personal matter. Moreover, you call all of us by our first names during touch base in an effort to give it a more personal feel. You called Dean Mr. Smith as you entered, feigning professionalism in my presence in an effort to make the situation sound urgent.”

 

Michael’s mouth laid slack at the wall of words. 

 

“Oh,” Cas remembered, “and the top of your shirt is unbuttoned. Whatever you came in to talk about, it’s personal. And I don’t think Dean wants to talk to you. But let’s not assume. Dean, do you want to talk personal matters with Michael?”

 

“No,” came the soft reply. 

 

“He doesn’t want to talk to you right now, sir,” Cas supplied, not breaking eye contact with the icy glare of the man standing at the door. 

 

Michael’s neck reddened as he struggled to hold in his rage. He clenched his fists at his side, breath heavy and mouth attempting to form words. With a huff, he stormed off with not so much as a goodbye, leaving the door ajar but the distinct sound of breaking ceramic and spilled pencils following him. 

 

Dean let out a sharp exhale, and he realized he had been holding in tension during Michael’s entire visit. He rubbed his face, trying to come down from the panic seeing him had induced. 

 

“Are you okay?” Cas asked sincerely. 

 

“I am now,” Dean breathed. 

 

Cas smiled and placed a gentle hand over Dean’s. “Would grabbing lunch away from this place make you feel better?”

 

Dean nodded, the idea sounding better the longer he considered. Besides, he was really enjoying Cas’ hand on his and could do for some more of that. He curled his fingers around Cas’ hand, and for the first time that day, he felt like today was going to be alright. 

 

“Yeah, I’d like that. Thanks for sticking your neck out there for me.”

 

Cas smiled and stood up, followed by Dean. “If he comes near you again I’ll bite his head off. I’ll put a sign up that says ‘back off’. A permanent sign.”

 

Dean laughed. “What, you gonna brand me or something?”

 

Cas clasped onto Dean’s shoulder as they left the office. “Yeah, sure. Something like that.”


	2. Operation Wing

**Summary for the Chapter:**

> Cas offers to take Dean under his wing, in order to learn how to handle uncomfortable work situations with his ex. But first, sex.

**Notes for the Chapter:**

> The prompts I combined today are: WING and It’s a Terrible Life AU! I immediately thought of this when I saw “wing” and I knew I could build on this existing It’s a Terrible Life story. Hope you enjoy! 
> 
> This is the chapter that made this ficlet jump from General Audiences to Explicit in a single bound. Not sorry.

Dean had gone on exactly two and a half dates with Cas — because the first thing was only lunch, on company time, so did it really count? — and he found himself falling hard. Cas had so much more to offer than ocean blue eyes and a voice that could make reading the phonebook sexy. Cas was supportive, trustworthy, and gentle.

Well, he was gentle until the bedroom door was locked. But Dean was totally okay with that.

He discovered very early on that Cas enjoyed being obeyed. But this was no power trip to make Dean feel inferior in order to puff himself up. In this moment, amid the sounds of Cas’ balls slapping against Dean’s ass as he railed into him, Dean felt more powerful than he ever had before. They were here, together, in perfect synchronicity, displaying how beautifully two bodies — no, two souls — could work together to reach bliss.

Cas dug his nails into Dean’s hips as he thrust relentlessly, brushing his prostate at every chance he could. Dean laid bent over the side of the bed, throat raw from constant cries of ecstasy. His cock rubbed the mattress roughly, soaking it in precome. His vision was growing spotty with the need to come.

“Please, Cas,” Dean begged. “Let me come. I need to… so bad.”

“Shhh,” Cas wisped as he reaches around to take Dean’s cock in his hand. “I know what you need, honey.”

Dean’s length throbbed in Cas’ hand, the sensation of warm skin enveloping him nearly sending him over the edge. “F-fuck, Cas!”

“That’s it,” he whispered in Dean’s ear as his own drives grew shallow. “Come for me now, Dean.”

“Ah, fuck,” Dean exclaimed, the wound up spring within him finally snapping. He covered Cas’ fist in his spend and listened to Cas’ last grumble before releasing into his hole. With a satisfied groan, Cas pulled out with a slick sound and brought his come-covered fingers to Dean’s mouth.

Dean had never tasted himself before. Hell, he hadn’t even been called “honey” before, but if it made Cas happy, it was happening. He took two of Cas’ fingers in his mouth and sucked. He swirled his tongue between the fingers and licked them clean, while Cas kissed his back from behind.

“So good,” Cas praised him. He removed his fingers from Dean’s mouth and turned him around before sitting them both on the bed. For the life of him, he couldn’t understand why anyone would treat this spectacular creature so poorly.

“We need to get going,” Dean noted. “Or we’re going to be late for the conference call.”

Cas left light kisses on the spots on Dean’s neck he had sucked bruises into. He took care to put them below his collar, especially with a touch base so close in the future. Clearly, Dean had no intention of enforcing their punctuality.

“Any idea of what the touch base will be about?” Cas asked, not wanting to mention his name.

“He’s gonna spout off some bullshit about being able to accept constructive criticism. Either that, or he’ll just go straight into how he doesn’t like you talking to me.”

“He said that to you?”

“Yeah,” Dean nodded, vividly remembering the day Cas called in sick. Michael wasted no time on replacing Cas as a presence surrounding Dean throughout the day. Dean found it suffocating when compared to how free Cas made him feel.

“I have an idea,” Cas began. “You see, when I was managing another company, we would role play to practice imaginary scenarios. Not that kind of role play,” he laughed at Dean’s wiggling eyebrows. “Now, the scenarios weren’t real. But learning to think on your feet is. It’s just as important in personal life as it is in business.”

“So you’ll what? Take me under your wing?”

“I like that term. Let’s call it that. Operation Wing: Dean learns comebacks and avoidance techniques to use on his abusive ex.”

Dean scooted closer to Cas on the bed. “You’re the best, Cas.”

“Let’s try one before conference call,” Cas suggested. “Okay, Dean. I’m Michael and I’ve cornered you in the break room asking where you hid the creamers. Because surely, it’s your fault, since you were the last one in the room.”

“I’d say fuck you, asshole!”

“Hmm, well that’s one way of doing it.” Cas was very, very good at what he did, and he was fresh out of a job that allowed him to use his specialized skill set to empower his people. He wanted to give Dean the same opportunity to thrive. Operation Wing was officially in session.


End file.
